6-Hydroxypicolinic acid

Bezeichnung:6-Hydroxypicolinic acid

CAS-Nr19621-92-2

Englisch Name:6-Hydroxypicolinic acid

CBNumberCB3712566

SummenformelC6H5NO3

Molgewicht139.11

MOL-Datei19621-92-2.mol

6-Hydroxypicolinic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	270 °C (dec.) (lit.)
Siedepunkt	436.0±45.0 °C(Predicted)
Dichte	1.451±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,Room Temperature
pka	3.29±0.20(Predicted)
Aggregatzustand	Powder
Farbe	Yellow to brown
BRN	115842
InChIKey	VRCWSYYXUCKEED-UHFFFAOYSA-N
CAS Datenbank	19621-92-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
HazardClass	IRRITANT
HS Code	29333990

Gefahreninformationscode (GHS)

6-Hydroxypicolinic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Light yellow Cryst
Verwenden
6-Hydroxypyridine-2-carboxylic acid may be used in the preparation of ruthenium(II) complex, [RuH(CO)(6-OH-py-2-COO)(PPh₃)₂].
Definition
ChEBI: 6-Hydroxypicolinic acid is an aromatic carboxylic acid and a member of pyridines.
Allgemeine Beschreibung
6-Hydroxypyridine-2-carboxylic acid (6HPA, 6-Hydroxypicolinic acid) is a picolinic acid derivative. It has been reported to exhibit enol-keto tautomerism. It is a chelating ligand exhibiting potential complexing ability (via N,O-chelation or N,O,O-chelation). Intramolecular proton transfer (IPT) in tautomeric forms of 6HPA has been investigated by density functional theory (DFT) calculations.
Synthese
6-Hydroxypicolinic acid is prepared by the reaction of 2-Bromo-6-hydroxypyridine and Carbon Dioxide. The specific synthesis steps are as follows:
To a solution of 2-bromo-6-hydroxypyridine (0.76 g, 4.4 mmol,1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of -PrMgCl in THF (2.2 mL,4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) wasadded dropwise during 5min, while maintaining the temperature below 20 C. The resultingmixture was stirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to20 C. The resulting mixture was warmed to 20 C in 0.5 h and quenched with water (6 mL).After stirring the mixture below 20 C for 10 min, the phases were separated and the water phasewas extracted one additional time with ethyl acetate. The resulting suspension was allowed to reachroom temperature and fitered through a mbox0.5 1 cm pad of silica gel eluted with 10 mL of ethylacetate. The ?ltrate was concentrated and the residue was puri?ed by ash chromatography on silicagel (eluent: petroleum ether/ethyl acetate = 10:1) to afford product 3m as off-white solid, 0.56 g (yield: 93percent) , m.p.: 275–277 C. 1H-NMR (600 MHz, DMSO) 7.56 (dd, J = 8.9, 7.0 Hz, 1H), 6.97 (d, J = 6.8 Hz,1H), 6.65 (d, J = 9.0 Hz, 1H). 13C-NMR (151 MHz, DMSO) 163.28, 162.67, 140.51, 137.97, 123.88, 110.42.

6-Hydroxypicolinic acid Upstream-Materialien And Downstream Produkte

6-Hydroxypicolinic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

19621-92-2, 6-Hydroxypicolinic acid Verwandte Suche:

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